Bobby played his high school football a Kingston High in North Carolina from 1989 to 1992. He started playing semi pro football in 1995 for the New Jersey Jaguars of the United Football League. He led the team with 52 tackles. In 1996 he joined the New Jersey Colts of the Atlantic Football League, and helped lead the team with 63 tackles and a birth in the a National Tournament before falling to the
powerful Marlboro Shamrocks. He played until 1997, then played college ball at William Paterson University, where he finished second on the team with 72 tackles, 5.5 sacks and 17 tackles for loss and a blocked punt. 1999 lead the school with 122 tackles. He was voted the New Jersey Athletic Conference "Co-Defensive Rookie of the Year", 1st team 1999 award winner and 1st team Eastern College Athletic Conference honors.
He then transfered and played at Rowan University where he played in 2000 and 2001, where he had another outstanding college career setting records for tackles for loss and forced fumbles. He was voted 2nd team Eastern College Athletic Conference honors. In 2002 he played semi pro football for the Newark Jets of the United Football League,which won the league championship. He made the league All Star team. 2004 played for the Orange County Bulldogs of the Empire Football League, and was voted "All League". In 2005 he played for the New Jersey Extreme of the Indoor Football League, making 51 tackles 2.5 sacks and 4 forced fumbles.
He also played for the Tri State Bulldogs semi pro team the same season and helped them to the league championship of the Empire League before losing. He has played for the Albany Metro Mallers of the EFL, and the New Jersey Buccaneers, leading them to the American Football League 2010 Harvest Bowl Championship and a loss in the title game to the New York Predators.